Cyclohexylamine → 6-(Cyclohexylamino)-6-oxohexanoic acid

HRID 486052

Reaction equation

C(O[C:4](=[O:12])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10])C.[CH:13]1([NH2:19])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>O>[CH:13]1([NH:19][C:4](=[O:12])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

Conditions

Temperature: 80 °C

Procedure

34.8 g (0.2 mol) of adipic acid monoethyl ester are added dropwise and with stirring to 19.8 g (0.2 mol) of cyclohexylamine. The temperature rises to 60° C. The reaction mixture is heated to 80° C. for 1 h. After cooling, the solution is poured into 200 ml of water and then extracted with 300 ml of ethyl ether. The ether phase is stirred into 150 ml of potassium hydrogen carbonate solution. After separation of the ether phase when settling has taken place, the aqueous phase is acidified to pH 1 with concentrated hydrochloric acid. The precipitate is drained, washed with water, dried and recrystallised in acetonitrile.

Workup

customrises to 60° C
temperatureAfter cooling
extractionextracted with 300 ml of ethyl ether
customAfter separation of the ether phase when
washwashed with water
customdried
customrecrystallised in acetonitrile

Sources & evidence

ORD record: ord-8b82665ebe884b4b9d2beb5211d8de2e
Source dataset: uspto-grants-1994_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05290790

Linked notes

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